ES2328671T3 - Compuestos de piperazilpirazinas como antagonistas del receptor de serotonina 5-ht2. - Google Patents

Compuestos de piperazilpirazinas como antagonistas del receptor de serotonina 5-ht2. Download PDF

Info

Publication number: ES2328671T3
Authority: ES; Spain
Prior art keywords: alkyl; hydrogen; methyl; compound; aryl
Prior art date: 2000-11-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES01983901T

Other languages

English (en)

Spanish (es)

Inventor

Bjorn M Nilsson

Martin Scobie

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Swedish Orphan Biovitrum AB

Original Assignee

Biovitrum AB

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-11-20

Filing date

2001-11-20

Publication date

2009-11-17

2000-11-20 Priority claimed from SE0004244A external-priority patent/SE0004244D0/xx

2001-11-20 Application filed by Biovitrum AB filed Critical Biovitrum AB

2009-11-17 Application granted granted Critical

2009-11-17 Publication of ES2328671T3 publication Critical patent/ES2328671T3/es

2021-11-20 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 86
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title claims abstract description 35
239000005557 antagonist Substances 0.000 title description 5
108091005479 5-HT2 receptors Proteins 0.000 title 1
108010072553 5-HT2C Serotonin Receptor Proteins 0.000 claims abstract description 19
102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims abstract description 19
229940076279 serotonin Drugs 0.000 claims abstract description 11
-1 methanesulfonamido, acetyl Chemical group 0.000 claims description 50
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 28
125000001072 heteroaryl group Chemical group 0.000 claims description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 22
238000000034 method Methods 0.000 claims description 20
208000035475 disorder Diseases 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 15
238000011282 treatment Methods 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
208000019901 Anxiety disease Diseases 0.000 claims description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
208000008589 Obesity Diseases 0.000 claims description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
235000020824 obesity Nutrition 0.000 claims description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
208000030814 Eating disease Diseases 0.000 claims description 7
208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
235000014632 disordered eating Nutrition 0.000 claims description 7
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000005251 aryl acyl group Chemical group 0.000 claims description 5
206010015037 epilepsy Diseases 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
201000009032 substance abuse Diseases 0.000 claims description 5
231100000736 substance abuse Toxicity 0.000 claims description 5
208000011117 substance-related disease Diseases 0.000 claims description 5
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
JOTZYRURFZTPHV-UHFFFAOYSA-N 4-[[3-[2-(3-piperazin-1-ylpyrazin-2-yl)oxyethoxy]phenyl]methyl]morpholine Chemical compound C=1C=CC(CN2CCOCC2)=CC=1OCCOC1=NC=CN=C1N1CCNCC1 JOTZYRURFZTPHV-UHFFFAOYSA-N 0.000 claims description 4
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239000004480 active ingredient Substances 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
125000005253 heteroarylacyl group Chemical group 0.000 claims description 4
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238000004519 manufacturing process Methods 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
201000000980 schizophrenia Diseases 0.000 claims description 4
231100000872 sexual dysfunction Toxicity 0.000 claims description 4
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
230000002485 urinary effect Effects 0.000 claims description 4
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
208000026139 Memory disease Diseases 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
230000001012 protector Effects 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
KYUMSNOGPIMDDQ-UHFFFAOYSA-N 2-[2-[3-[(4-methylpiperazin-1-yl)methyl]phenoxy]ethoxy]-3-piperazin-1-ylpyrazine Chemical compound C1CN(C)CCN1CC1=CC=CC(OCCOC=2C(=NC=CN=2)N2CCNCC2)=C1 KYUMSNOGPIMDDQ-UHFFFAOYSA-N 0.000 claims description 2
IMGWDNKFCPQHLO-UHFFFAOYSA-N 2-piperazin-1-yl-3-[2-[3-(pyrrolidin-1-ylmethyl)phenoxy]ethoxy]pyrazine Chemical compound C=1C=CC(CN2CCCC2)=CC=1OCCOC1=NC=CN=C1N1CCNCC1 IMGWDNKFCPQHLO-UHFFFAOYSA-N 0.000 claims description 2
150000004677 hydrates Chemical class 0.000 claims description 2
SGQNDQAVSJOBEL-UHFFFAOYSA-N n-[[3-[2-(3-piperazin-1-ylpyrazin-2-yl)oxyethoxy]phenyl]methyl]propan-2-amine Chemical compound CC(C)NCC1=CC=CC(OCCOC=2C(=NC=CN=2)N2CCNCC2)=C1 SGQNDQAVSJOBEL-UHFFFAOYSA-N 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
239000012453 solvate Substances 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
USDIRSJFHPHMAS-UHFFFAOYSA-N ClC1=NC=C(C=2C1=NC=CN=2)F Chemical compound ClC1=NC=C(C=2C1=NC=CN=2)F USDIRSJFHPHMAS-UHFFFAOYSA-N 0.000 claims 1
125000002393 azetidinyl group Chemical group 0.000 claims 1
235000005686 eating Nutrition 0.000 claims 1
239000003446 ligand Substances 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
239000000556 agonist Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000018 receptor agonist Substances 0.000 description 7
229940044601 receptor agonist Drugs 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
102000005962 receptors Human genes 0.000 description 6
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239000002904 solvent Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
230000036506 anxiety Effects 0.000 description 5
210000003169 central nervous system Anatomy 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
229940079593 drug Drugs 0.000 description 5
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 4
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
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230000037396 body weight Effects 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
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239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IJINSJSWDSHUBL-UHFFFAOYSA-N tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC=CN=C1Cl IJINSJSWDSHUBL-UHFFFAOYSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
CZDVJGBXKADLCY-UHFFFAOYSA-N thieno[3,4-b]pyrazine Chemical compound N1=CC=NC2=CSC=C21 CZDVJGBXKADLCY-UHFFFAOYSA-N 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Diabetes (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ES01983901T 2000-11-20 2001-11-20 Compuestos de piperazilpirazinas como antagonistas del receptor de serotonina 5-ht2. Expired - Lifetime ES2328671T3 (es)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
SE2000104244		2000-11-20
SE0004244A SE0004244D0 (sv)	2000-11-20	2000-11-20	Novel compounds and their use
US25370200P	2000-11-28	2000-11-28
US253702P		2000-11-28

Publications (1)

Publication Number	Publication Date
ES2328671T3 true ES2328671T3 (es)	2009-11-17

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ES01983901T Expired - Lifetime ES2328671T3 (es)	2000-11-20	2001-11-20	Compuestos de piperazilpirazinas como antagonistas del receptor de serotonina 5-ht2.

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EP (1)	EP1337518B1 (de)
JP (1)	JP4204315B2 (de)
KR (1)	KR100831909B1 (de)
CN (1)	CN1227237C (de)
AT (1)	ATE433962T1 (de)
AU (1)	AU1529402A (de)
BR (1)	BR0115436A (de)
CA (2)	CA2449899C (de)
DE (1)	DE60139021D1 (de)
DK (1)	DK1337518T3 (de)
EA (1)	EA005975B1 (de)
ES (1)	ES2328671T3 (de)
IL (2)	IL155875A0 (de)
MX (1)	MXPA03004391A (de)
NO (1)	NO325321B1 (de)
NZ (1)	NZ525699A (de)
PL (1)	PL360982A1 (de)
WO (1)	WO2002040457A1 (de)

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ES2252004T3 (es)	1999-05-21	2006-05-16	Biovitrum Ab	Nuevos compuestos, su uso y preparacion.
MXPA01012914A (es)	1999-06-15	2004-04-21	Bristol Myers Squibb Co	Gama-carbolinas fundidas de heterociclo substituido.
JP2003506369A (ja)	1999-07-29	2003-02-18	イーライ・リリー・アンド・カンパニー	セロトニン作動性のベンゾフラン
DE60004066T2 (de)	1999-07-29	2004-04-15	Eli Lilly And Co., Indianapolis	Benzofurylpiperazine: 5-ht2c serotoninrezeptor agonisten
JP2003506371A (ja)	1999-07-29	2003-02-18	イーライ・リリー・アンド・カンパニー	セロトニン作動性ベンゾチオフェン
DE60002583T2 (de)	1999-07-29	2004-03-25	Eli Lilly And Co., Indianapolis	Benzofurylpiperazine als serotonin-agonisten
GB9918962D0 (en)	1999-08-11	1999-10-13	Cerebrus Ltd	Chemical compounds xxii
GB9918965D0 (en)	1999-08-11	1999-10-13	Cerebrus Ltd	Chemical compounds xxi

2001
- 2001-11-20 EP EP01983901A patent/EP1337518B1/de not_active Expired - Lifetime
- 2001-11-20 CN CNB018192416A patent/CN1227237C/zh not_active Expired - Fee Related
- 2001-11-20 WO PCT/SE2001/002570 patent/WO2002040457A1/en not_active Ceased
- 2001-11-20 PL PL36098201A patent/PL360982A1/xx unknown
- 2001-11-20 NZ NZ525699A patent/NZ525699A/en unknown
- 2001-11-20 DK DK01983901T patent/DK1337518T3/da active
- 2001-11-20 CA CA2449899A patent/CA2449899C/en not_active Expired - Fee Related
- 2001-11-20 JP JP2002542785A patent/JP4204315B2/ja not_active Expired - Fee Related
- 2001-11-20 DE DE60139021T patent/DE60139021D1/de not_active Expired - Lifetime
- 2001-11-20 CA CA002428905A patent/CA2428905A1/en active Pending
- 2001-11-20 EA EA200300595A patent/EA005975B1/ru not_active IP Right Cessation
- 2001-11-20 KR KR1020037006822A patent/KR100831909B1/ko not_active Expired - Fee Related
- 2001-11-20 IL IL15587501A patent/IL155875A0/xx active IP Right Grant
- 2001-11-20 AT AT01983901T patent/ATE433962T1/de not_active IP Right Cessation
- 2001-11-20 ES ES01983901T patent/ES2328671T3/es not_active Expired - Lifetime
- 2001-11-20 BR BR0115436-2A patent/BR0115436A/pt not_active IP Right Cessation
- 2001-11-20 AU AU1529402A patent/AU1529402A/xx not_active Withdrawn
- 2001-11-20 MX MXPA03004391A patent/MXPA03004391A/es active IP Right Grant
2003
- 2003-05-12 IL IL155875A patent/IL155875A/en not_active IP Right Cessation
- 2003-05-19 NO NO20032253A patent/NO325321B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
EA200300595A1 (ru)	2003-10-30
EA005975B1 (ru)	2005-08-25
CN1227237C (zh)	2005-11-16
JP4204315B2 (ja)	2009-01-07
IL155875A0 (en)	2003-12-23
BR0115436A (pt)	2004-01-06
DE60139021D1 (de)	2009-07-30
CA2449899C (en)	2010-04-06
EP1337518B1 (de)	2009-06-17
WO2002040457A1 (en)	2002-05-23
NO325321B1 (no)	2008-03-31
DK1337518T3 (da)	2009-10-19
HK1066810A1 (en)	2005-04-01
ATE433962T1 (de)	2009-07-15
NO20032253L (no)	2003-07-18
NZ525699A (en)	2005-03-24
NO20032253D0 (no)	2003-05-19
CA2428905A1 (en)	2002-05-23
EP1337518A1 (de)	2003-08-27
KR100831909B1 (ko)	2008-05-26
CN1520404A (zh)	2004-08-11
MXPA03004391A (es)	2004-05-31
KR20030060946A (ko)	2003-07-16
PL360982A1 (en)	2004-09-20
IL155875A (en)	2007-06-17
JP2004531465A (ja)	2004-10-14
AU1529402A (en)	2002-05-27
CA2449899A1 (en)	2002-05-23

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